I stared up at Jackson, doing my best to look him square in the eye while trying to decide if he was being serious or not. I couldn’t quite believe my ears but then this was Jackson, so anything was possible.
“We’d have a great time – sun, sand, too much wine – and some amazing, adventurous sex! C’mon, it’s time you got back out there. Come with me!”
Jackson is my housemate. Well, more my landlord really. It’s meant to be temporary but it seems to be lasting a very long time. I left an unhappy and unrewarding marriage four months ago, flat broke and with no prospect of getting a place of my own for a while. Jackson was a work friend who lived alone. He offered me his spare room at a ridiculously cheap rate, and I really didn’t see any other options.
It may seem simple and you’re probably thinking what a nice guy this Jackson must be. Well, yes he is pretty nice actually but he is also extremely promiscuous, loves himself a bit too much, has no idea about boundaries or rules, and has been trying his best to get in my panties since the day I met him four years ago!
He’s 6’2”, salt and pepper hair, brown eyes the shade of dark chocolate, tanned skin and has MASSIVE arms, back and chest. He must lift serious weights at the gym. Give him an audience and he can be completely over the top – a loud braggart with far too much to say. Spend some time one to one, however, and he is lovely. He is intelligent, funny, and even sweet. In the right mood he can soften his voice down to a deep, sexy rumble which sends naughty shivers up and down my spine.
By contrast I am really small. I’m 5’3” with a petite build, long chestnut hair and brown eyes. I would describe myself as the typical ‘girl next door’. I don’t do dressing up, I don’t wear make-up and I don’t bother with loads of scent . . . but for some reason Jackson has been absolutely clear from the beginning that we should get naked together!
Since I moved in he has been quite the gentleman, I guess sensing that I needed some recovery time following the stress of this winter but it looks like his patience has run out. In short, his proposition is that I accompany him on holiday to his mate’s villa in Spain (at his expense) where the three of us will enjoy the sun, sand and Sangria – and also a lot of hot action by the pool. For me, as he explains, the benefits are clear - a free holiday and the opportunity to ‘get back out there’.
My reaction to this is mixed. On the one hand I am outraged! He is basically offering to pay me for a week of sex with him while sharing me with his friend. On the other hand I cannot deny that right at this moment, as his offer sinks in, there is a definite dampness spreading in my panties at the thought of being used
in this way. I picture lounging naked by the pool being licked and sucked by this gorgeous, experienced man while his mate watches and waits his turn.
He is watching me intently, assessing how far to push. Am I going to give in??? I take a deep breath, do my best to be cool and say, “OK”
My eyes flick open and I stretch in luxurious comfort. It takes a moment to remember where I am – the sun is streaming in through the windows of a big airy room. White muslin drapes billow slightly in the warm scented breeze which flows through the room. I can smell sage, thyme and . . . coffee! I sit up in a huge white bed in which I have clearly slept alone. We got in late last night after the short flight from Manchester to Alicante and were met by Nick, Jackson’s friend. He’s pretty cute too – 5’ 9”, already grey hair but with a youthful tanned face, mischievous eyes and a ready smile. I think I’ll like him.
Truth be told I’m a bit nervous but I really want a cup of that coffee I can smell so I pull on some shorts and a bikini top and follow my nose.
“Here she is!” Jackson announces to the world at large. “I was beginning to hope I would have to come and wake you up” he gives me a playful leer while simultaneously wrapping me tightly in a cuddle. He does this – combines warm affection and basic loveliness with an ‘I want to get in your knickers’ philosophy. I can never decide if he’s just very skilled at getting what he wants from women or if he does actually care for me. Who knows, and to a point, who cares??
“Hi, good morning . . . is any of that coffee for me?” I say.
“Here you go . . . “ Nick hands me a cup and gestures to a platter of fruit and other breakfast bits and pieces. I settle down in a comfy chair and take it all in. The terrace is lovely, very private with lush planting all around and an inviting pool sparkling in the centre. There is plenty of furniture to choose from and I spot an outdoor shower tucked into the shrubbery. I smile inwardly – I’m sure we’ll be having some fun with that!!
It’s mid-afternoon, siesta time. All around the villa the landscape is languishing in the heat. Even the birds and the crickets are silent. I’m stretched out on my tummy on a sun bed, deliciously comfortable in my bikini. I hear flip flops approaching and someone sits down on the next door sun bed. Jackson is so gorgeous - tanned body on show, a dusting of dark hair on his chest which I can follow southwards. He has a white towel wrapped around his hips . . . and at this realisation my heart stutters slightly. Muscles clench and nerves flutter in my stomach but at the same time I can feel a slight throbbing begin between my legs. I do want this, after all. I’m completely turned on but just a bit nervous that I somehow won’t live up to all these years of anticipation on Jackson’s part.
He holds up a bottle of sun tan lotion to show me, then steps over and unties the strings of my white bikini top. Pouring some lotion into his hands he begins to smooth it into my shoulders and down my back, stroking every inch with those big capable hands. I’m enjoying the sensation very much as he works the lotion right down to my behind. “I don’t think you’ll need these” he says in his most sexy rumble as he very deliberately unties the side strings of my bottoms. The fabric falls away and I am stark naked on the bed beneath him.
He murmurs his approval and pours a little more lotion into his hands. This time he begins at my ankles and ever so slowly works his way up my legs, smoothing his palms around and around. Above the sensitive skin at the back of my knees he pauses and coaxes my legs slightly apart. I am beginning to breathe erratically as my arousal grows. Higher and higher go his hands, brushing ever closer to my sex. He tantalises and teases and I grow frustrated. I am pushing my behind up into his hands begging him to touch me properly. Abruptly he flips me over onto my back and pushes two well oiled fingers deep inside me. I gasp and moan with pleasure and grind against his hand.
Jackson fastens his mouth onto my bullet hard nipples, one after the other. He is breathing heavily and murmuring a torrent of words to me – exactly how much he wants this, how long he’s wanted to do it, how much he wants to make me come and all the ways he’s going to do it. I am awash with sensation, my skin tingles everywhere he visits with his mouth and all the while he is pushing his fingers in and out of me with relentless pace. Abstractly I notice how the muscles in his arms and shoulders bunch and contract while a groundswell builds in me. I arch my back and let go, exploding around his fingers. The orgasm goes on and on, just on the edge between painful and exquisite.
I can see how hard he is under that towel so I reach up and tug on the knot. The towel falls to the floor and I get my first view of Jackson’s proudly upright cock. Like everything else about him it’s big, exuberant and in my face! While I’m deciding what to do with him there is a cheer from across the pool and Nick heads over to join us. He is already pulling off his shorts and he is also rock hard and ready to play.
Jackson straddles the sun bed and reaches for me. Frankly I don’t need to be asked twice – I scoot along the bed and let him lift me against that magnificent strong chest. I feel the end of his cock pushing against me and he impales me, filling me to his balls. I gasp, still tight from my orgasm, and I feel as much as hear the deep satisfied rumble in his chest.
Nick has straddled the sun bed too, sitting close behind me and now he reaches round and takes my breasts in his hands, fondling and stroking the sensitive skin. He trails his tongue across the warm skin of my shoulder and I can feel his erection pressing into the small of my back. I give myself over completely to the ministrations of these two delicious men, leaning back into Nick and pressing my breasts into his hands. Doing so gives Jackson space to move, easing the long length of his cock in and out of my tight, dripping pussy.
Moving away Nick pulls me down so that I am lying flat on the bed, my legs wrapped around Jackson. A shadow falls across my face and the velvet end of Nick’s rock hard cock nudges at my lips. I gasp and open my mouth, reaching for him with my tongue. He is soon fucking my mouth while Jackson picks up the pace, driving hard into me. Both men keep up a steady stream of encouragement and groans of pleasure as we shift positions slightly, a little harder, a little softer – this way and that - we’re all caught up in the heat and passion of this three way fuck.
I feel completely wanton and like I never want this to end. Without much warning Nick explodes into my mouth spurting warm cum across my tongue. I swallow happily, knowing how much it will turn on Jackson who has watched this performance from his position between my legs. I grin wickedly at him and sure enough I feel him tense up and I watch as his face contorts and he empties himself deep inside me.
My body is singing to me as I lie back in the warmth, not a trace of self consciousness left. Jackson crouches down and kisses me deeply, his tongue rubbing gently along with mine. He chuckles, delighted with me, with the situation in general. He scoops me up off the bed and we slip into the cool waters of the pool. I know exactly what I want from him next . . . and it won’t be long before I want it!
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/novels/the-holiday-part-one.aspx">The Holiday part one</a>